Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

1,2-Diaryl-1,2-disodioethanes: Versatile, Highly Reactive, and Tunable Synthetic Equivalents of Sodium Metal

Ugo Azzena
+ Author Affiliations
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Dipartimento di Chimica e Farmacia, Università di Sassari, via Vienna 2, I-07100 Sassari, Italy. Email: ugo@uniss.it

Australian Journal of Chemistry 70(6) 647-651 https://doi.org/10.1071/CH16601
Submitted: 25 October 2016  Accepted: 18 November 2016   Published: 14 December 2016

Abstract

1,2-Diaryl-1,2-disodioethanes are easily prepared, versatile, and stable diorganometals finding application in 1,2-reductive eliminations as well as in the degradation of several persistent organic pollutants as homogeneous synthetic equivalents of a highly reactive form of Na metal. Understanding their reactivity in terms of their different electron-donor power, which is strongly affected by the nature of substituents located either on the aromatic ring(s) or on the carbanionic centers, allowed rationalization of their employment not only as chemoselective single electron transfer reducing reagents, but also as bases in the generation of enediolates of arylacetic acids bearing easily reducible carbon–halogen bonds.


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